Journal of Organic Chemistry Research, Journal Year: 2023, Volume and Issue: 11(01), P. 1 - 9
Published: Jan. 1, 2023
Language: Английский
Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 13, 2024
Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.
Language: Английский
Citations
28
Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(24), P. 6999 - 7015
Published: Jan. 1, 2022
This review summarizes the recent advances in synthetic application of iodonium ylides covering 2017 to 2022.
Language: Английский
Citations
39
Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(1), P. 24 - 38
Published: Nov. 23, 2022
The metal-catalyzed successive activation and functionalization of arene/heteroarene is one the most fundamental transformations in organic synthesis leads to privileged scaffolds natural products, pharmaceuticals, agrochemicals, fine chemicals. Particularly, transition-metal-catalyzed C-H arenes with carbene precursors via metal migratory insertion has been well studied. As a result, diverse have evaluated, such as diazo compounds, sulfoxonium ylides, triazoles, etc. In addition, there significant developments use iodonium ylides recent years, these reactions proceed high efficiencies selectivities. This review provides comprehensive overview functionalizations, including scope, limitations, their potential synthetic applications.
Language: Английский
Citations
27
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8360 - 8368
Published: June 1, 2023
A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis 6-arylated phenanthridines. This is first example employing as aryl radical sources in a visible-light-induced cyclization reaction.
Language: Английский
Citations
13
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 5, 2025
A tandem Hexadehydro-Diels–Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which served as a unique double bond and reacted aryne to form four-membered iodonium(III) cycle, then converted iodoarene after aryl group from iodine adjacent carbon. This strategy allows the efficient construction fully substituted compounds.
Language: Английский
Citations
0
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(27), P. 5567 - 5586
Published: Jan. 1, 2023
Efficacious protocols have been established to synthesize a structurally privileged Π-extended coumarin-fused pyridone nucleus by activating the vinylic C(sp2)-H bond of coumarin-3-carboxamide under influence inexpensive Ru(II)-metal. Here an N-methoxy carboxamide entity has exploited as chelating fragment manifest functionalization with concomitant (4 + 2) annulation reaction, resulting in heterocyclic ring-forming along sulfoxonium ylide and iodonium representative bench-stable carbene surrogates. This diverse heterocycle formation via insertion strategies, is further expanded activate ortho-C(sp2)-H bonds different heterocycles employing sp2-N moiety directing group develop acyl-alkylated/alkenylated quinazolines, isoxazoles highly fluorescent pyridone-N-oxides. Intriguingly, during evaluation versatility current protocols, one-pot double C-H activation rationalized presence ylide, which results biologically potent benzimidazole-fused coumarin-centered bridge-headed polycyclic heteroarenes. Furthermore, chemo-selective late-stage synthetic transformation being designed differently substituted analogues switching nature reducing agent. In addition, photophysical experiment was done on one pyridine-N-oxide compound (7e) delightfully it exhibited fluorescence quenching activity selectively Al3+ ions, appears be unique feature our methodology. Finally, upon correlation merit developed pathways, mediated strategy superior.
Language: Английский
Citations
9
Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3567 - 3567
Published: July 29, 2024
Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal migratory insertion processes. Among precursors, iodonium ylides serve as novel emerging precursor features including easy accessibility, thermal stability high activity, which have attracted great attention from organic chemists achieved tremendous success in transformation. In this review, recent progress on the application multifunctional coupling characteristics bond activation reactions is summarized, potential discussed.
Language: Английский
Citations
1
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(35), P. 7121 - 7127
Published: Jan. 1, 2024
We introduced, for the first time, N -methoxyamide directed proximal C–H bond activation of imidazo[1,2- a ]pyridines C(sp 2 )–C(sp ) formation via transition metal catalysed approach to obtain C-5 arylated ]pyridines.
Language: Английский
Citations
0
Polyhedron, Journal Year: 2024, Volume and Issue: unknown, P. 117260 - 117260
Published: Oct. 1, 2024
Language: Английский
Citations
0
Synthesis, Journal Year: 2023, Volume and Issue: 56(12), P. 1815 - 1842
Published: Nov. 6, 2023
Abstract In the realm of synthetic organic chemistry, catalysis directed C–H activation by transition metals is an outstanding and efficient method for synthesis natural products, materials, fundamental building blocks. Notably, this strategy has experienced remarkable advances in recent years, particularly its application to various substrate classes, including essential indole scaffold. Indole a highly sought-after target chemistry. The significance extends beyond use total drug discovery. It also serves as important tool development pharmaceutical agents, agrochemicals, materials. By targeting indole, chemists can access wide range bioactive compounds, which opens new avenues chemical biology research. structurally varied indoles been greatly aided comprehensive toolkit made possible versatile functionalization platform. This review highlights latest breakthroughs rhodium-catalyzed at C2, C4, C7 positions These developments represent significant progress field hold promising potential further indole-based compounds. 1 Introduction 2 Development Rhodium-Catalyzed Activation 3 General Mechanistic Rh(III)-Catalyzed 4 Direct Functionalization Indoles 4.1 C2 4.2 C4 4.3 Dual Strategy 4.4 5 Conclusion
Language: Английский
Citations
1